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2-Aminobenzaldehyde is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C6H4(NH2)CHO. It is one of three isomers of aminobenzaldehyde. It is a low-melting yellow solid that is soluble in water.
Preparation and reactions
It is usually prepared by reduction of 2-nitrobenzaldehyde with iron oriron(II) sulfate
Iron(II) sulfate (British English: iron(II) sulphate) or ferrous sulfate denotes a range of salts with the formula Fe SO4·''x''H2O. These compounds exist most commonly as the heptahydrate (''x'' = 7) but several values for x are know ...
. Like related aminoaldehydes, it is unstable with respect to self-condensation Self-condensation is an organic reaction in which a chemical compound containing a carbonyl group acts both as the electrophile and the nucleophile in an aldol condensation. It is also called a symmetrical aldol condensation as opposed to a mixed ...
.
2-Aminobenzaldehyde is used to prepare quinoline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only sli ...
s by the Friedländer synthesis
The Friedländer synthesis is a chemical reaction of 2-aminobenzaldehydes with ketones to form quinoline derivatives. It is named after German chemist Paul Friedländer (1857–1923).
This reaction has been catalyzed by trifluoroacetic acid, ...
:
By template reaction
In coordination chemistry, a template reaction is any of a class of ligand-based reactions that occur between two or more adjacent coordination sites on a metal center. In the absence of the metal ion, the same organic reactants produce different ...
s, it also forms trimeric and tetrameric condensation products that have been studied as ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
s.
References